Hydrochloric Acid → HCID 10673130, compound

HRID 1645786Notes

Reaction equation

HRID 1645786 reaction equation
[CH3:1][O:2][C:3]([CH2:5][CH2:6][CH:7]([CH2:20][S:21]([C:24]1[CH:33]=[CH:32][C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=1)(=[O:23])=[O:22])[C:8]([N:10]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:11][C:12]([OH:14])=O)=[O:9])=[O:4].Cl.[CH3:35][NH:36][CH3:37].C(P(=O)(OCC)OCC)#N.Cl>CN(C)C=O.C(N(CC)CC)C>[CH3:35][N:36]([CH3:37])[C:12]([CH2:11][N:10]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:8]([CH:7]([CH2:20][S:21]([C:24]1[CH:33]=[CH:32][C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=1)(=[O:22])=[O:23])[CH2:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])=[O:9])=[O:14]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10473Dimethylamine, hydrochlorideHCID 76257Diethyl cyanophosphonateHCID 10790794HCID 10790794, compound

Product 1

HCID 10673130HCID 10673130, compoundYield 89.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of N-[2-(2-methoxycarbonylethyl)-3-(2-naphthylsulfonyl)propionyl]-N-pentylglycine (100 mg), dimethylamine hydrochloride (21 mg), and triethylamine (70 μl) in N,N-dimethylformamide (1 ml) was added diethyl cyanophosphonate (42 μl) at 0° C. After stirring at room temperature for 16 hours, a dilute hydrochloric acid was added, and the reaction mixture was extracted with ethyl acetate. The organic layer was washed with a saturated sodium bicarbonate solution and water, dried over MgSO4, and evaporated at reduced pressure. The residue was purified by flash column chromatography on silica eluting with chloroform/methanol (15:1) to give 95 mg of methyl 4-[N-(N,N-dimethylcarbamoylmethyl)-N-pentylcarbamoyl]-5-(2-naphthylsulfonyl)pentanoate as oil. ##STR19##

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with a saturated sodium bicarbonate solution and water
  3. dry with materialdried over MgSO4
  4. customevaporated at reduced pressure
  5. customThe residue was purified by flash column chromatography on silica eluting with chloroform/methanol (15:1)

Sources & evidence

ORD record
ord-b408b26331b64c1a83180e03695fb683
Source dataset
uspto-grants-1993_01
Patent number
US05177069

Reaction notes

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